Water → HCID 86689404, compound

HRID 926663Notes

Reaction equation

HRID 926663 reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([CH:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH:32]=O)[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].O>ClCCl>[Br:2][C:1]([Br:5])=[CH:32][CH:31]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 153334732-Hexyldecanal

Product 1

HCID 86689404HCID 86689404, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Carbon tetrabromide (218 g, 657 mmol) is dissolved in anhydrous dichloromethane (1600 cm3) and cooled to 0° C. Triphenylphosphine (345 g, 1.32 mol) is added in one portion, the mixture exothermed to 15° C. and is re-cooled to 0° C., whilst stirring for 45 minutes. 2-Hexyldecan-1-al (Price, S. C.; Stuart, A. C.; You, W.; Macromolecules 2010, 43, 797-804) (79.0 g, 329 mmol) is added dropwise over 45 minutes and the mixture is allowed to warm to 23° C. After 2 hours, the reaction mixture is carefully poured into water (2000 cm3), the organic phase is separated, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product is dissolved in dichloromethame (2000 cm3) and passed twice through a plug of silica eluting with petroleum ether (40-60° C.) to yield the title product as a pale yellow oil (117.4 g, Yield: 90%). NMR (1H, 400 MHz, CDCl3): δ 6.15 (d, J=9.6 Hz, 1H); 2.38 (m, 1H); 1.29 (m, 24H); 0.91 (m, 6H).

Workup

  1. customexothermed to 15° C.
  2. temperatureis re-cooled to 0° C.
  3. additionMacromolecules 2010, 43, 797-804) (79.0 g, 329 mmol) is added dropwise over 45 minutes
  4. temperatureto warm to 23° C
  5. waitAfter 2 hours
  6. customthe organic phase is separated
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. dissolutionThe crude product is dissolved in dichloromethame (2000 cm3)
  11. custompassed twice through a plug of silica eluting with petroleum ether (40-60° C.)

Sources & evidence

ORD record
ord-18ca40a867604b3cbdb473ee780934a7
Source dataset
uspto-grants-2016_03
Patent number
US09287504B2

Reaction notes

Loading…